Sodium hydride → 3-{1-[(3-propylimidazo[1,2-a]pyridin-2-yl)methyl]-1H-imidazol-2-yl}benzonitrile

HRID 586373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 586373
[H-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([C:11]2[NH:12][CH:13]=[CH:14][N:15]=2)[CH:8]=[CH:9][CH:10]=1)#[N:4].Cl[CH2:17][C:18]1[N:19]=[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]2[C:26]=1[CH2:27][CH2:28][CH3:29]>CN(C=O)C>[CH2:27]([C:26]1[N:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]2=[N:19][C:18]=1[CH2:17][N:15]1[CH:14]=[CH:13][N:12]=[C:11]1[C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:3]#[N:4])[CH2:28][CH3:29]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 223350602-Chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridineHCID 223350823-(1H-Imidazol-2-yl)benzonitrile

Produkt 1

HCID 208256803-{1-[(3-propylimidazo[1,2-a]pyridin-2-yl)methyl]-1H-imidazol-2-yl}benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NaH (13.5 mg of 60% wt., 0.34 mmol) is added to a solution of 3-cyano-(1H-imidazol-2-yl)benzene (57.2 mg, 0.34 mmol) in anhydrous DMF (3.5 mL). After 15 minutes, 2-chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine (70.5 mg, 0.34 mmol) is added and the reaction mixture is stirred at ambient temperature for 18 hours. Concentration at reduced pressure followed by purification by chromatography on silica gel (5% MeOH/CHCl3) provides 3-{1-[(3-propylimidazo[1,2-a]pyridin-2-yl)methyl]-1H-imidazol-2-yl}benzonitrile as a light yellow solid. TLC (5% MeOH/CHCl3) Rf=0.50. 1H NMR (CDCl3): 8.13, s (1H); 8.07, d (1H); 7.90, d (1H); 7.71, d (1H); 7.60, d (1H); 7.58, d (1H); 7.20, dd (1H); 7.14, bs (2H); 6.85, t (1H); 5.32, s (2H); 2.70, t (2H); 1.50, p (2H), 0.90, t (3H). LRMS m/z (M+1) 342.30.

Aufarbeitung

  1. concentrationConcentration at reduced pressure
  2. customfollowed by purification by chromatography on silica gel (5% MeOH/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-06c4efba44ac47e58c27ce557ec844a2
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936617B2

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